WO2004004480A1 - Gomme a macher moderee de resine comprimee - Google Patents

Gomme a macher moderee de resine comprimee Download PDF

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Publication number
WO2004004480A1
WO2004004480A1 PCT/DK2003/000465 DK0300465W WO2004004480A1 WO 2004004480 A1 WO2004004480 A1 WO 2004004480A1 DK 0300465 W DK0300465 W DK 0300465W WO 2004004480 A1 WO2004004480 A1 WO 2004004480A1
Authority
WO
WIPO (PCT)
Prior art keywords
chewing gum
gum
gum base
weight
amount
Prior art date
Application number
PCT/DK2003/000465
Other languages
English (en)
Inventor
Bitten Thorengaard
Dorthe Schackinger Boesen
Vibeke Nissen
Original Assignee
Gumlink A/S
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from PCT/DK2002/000461 external-priority patent/WO2004004478A1/fr
Priority claimed from PCT/DK2002/000462 external-priority patent/WO2004004479A1/fr
Priority to DE60321916T priority Critical patent/DE60321916D1/de
Priority to KR1020047021653A priority patent/KR101109155B1/ko
Priority to JP2004518467A priority patent/JP5133499B2/ja
Priority to EA200500128A priority patent/EA008845B1/ru
Application filed by Gumlink A/S filed Critical Gumlink A/S
Priority to AU2003243931A priority patent/AU2003243931A1/en
Priority to MXPA04012405A priority patent/MXPA04012405A/es
Priority to EP03762473A priority patent/EP1523241B1/fr
Priority to CA2491350A priority patent/CA2491350C/fr
Priority to DK03762473T priority patent/DK1523241T3/da
Publication of WO2004004480A1 publication Critical patent/WO2004004480A1/fr
Priority to US11/028,684 priority patent/US20050175733A1/en
Priority to US13/352,211 priority patent/US20120114789A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/0002—Processes of manufacture not relating to composition and compounding ingredients
    • A23G3/0004—Processes specially adapted for manufacture or treatment of sweetmeats or confectionery
    • A23G3/0019—Shaping of liquid, paste, powder; Manufacture of moulded articles, e.g. modelling, moulding, calendering
    • A23G3/0025—Processes in which the material is shaped at least partially in a mould in the hollows of a surface, a drum, an endless band, or by a drop-by-drop casting or dispensing of the material on a surface, e.g. injection moulding, transfer moulding
    • A23G3/004—Compression moulding of paste, e.g. in the form of a ball or rope or other preforms, or of a powder or granules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/02—Apparatus specially adapted for manufacture or treatment of chewing gum
    • A23G4/04—Apparatus specially adapted for manufacture or treatment of chewing gum for moulding or shaping
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/02—Apparatus specially adapted for manufacture or treatment of chewing gum
    • A23G4/04—Apparatus specially adapted for manufacture or treatment of chewing gum for moulding or shaping
    • A23G4/043—Apparatus specially adapted for manufacture or treatment of chewing gum for moulding or shaping for composite chewing gum
    • A23G4/046—Apparatus specially adapted for manufacture or treatment of chewing gum for moulding or shaping for composite chewing gum with a centre made of chewing gum
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/064—Chewing gum characterised by the composition containing organic or inorganic compounds containing inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/08—Chewing gum characterised by the composition containing organic or inorganic compounds of the chewing gum base
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/12—Chewing gum characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
    • A23G4/126—Chewing gum characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins containing vitamins, antibiotics
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/18—Chewing gum characterised by shape, structure or physical form, e.g. aerated products
    • A23G4/20—Composite products, e.g. centre-filled, multi-layer, laminated

Definitions

  • the present invention relates to chewing gum granules and chewing gum made on the basis of such chewing gum granules.
  • the different processes may be overall categorized in basically two different processes; that is chewing gum mechanically mixed on the basis of a gum base compounds or chewing gum compressed on the basis of more or less discrete gum base particles.
  • the first type of chewing gum generally benefits from a very comfortable texture, among several different parameters, most likely due to the mechanically mixing of the polymers and for example the flavors.
  • One disadvantage of such type of process and chewing gum is, however, that the different ingredients, such as encapsulated flavor, active ingredients, etc. may be more or less destroyed or degraded by the mixing process.
  • the second type of chewing gum generally benefits from a relatively gentle handling of vulnerable additives, such as the above-mentioned flavors or active ingredients.
  • vulnerable additives such as the above-mentioned flavors or active ingredients.
  • One disadvantage of such type of chewing gum is, however, that the resulting chewing gum tablet may typically disintegrate too easy, especially during the initial chew of the gum.
  • WO 03/011045 discloses a technique where the sticking or adhering of the chewing gum mixture to the tableting process equipment is dealt with by controlling the size of the mixture granules. It is one object of the invention to provide a chewing gum compression chewing gum composition, which, when processed by means of compression, provides a texture like conventionally mixed chewing gum.
  • the invention relates to a gum base granule comprising
  • a granule is understood as a small particle whole or completely formed by gum base or derivatives thereof.
  • granules in large numbers form a granule mixture, made by granulation e.g. by known processes of a gum base "raw material".
  • the gum base granule mixture may typically directly or after pre-processing be compressed to form a tableted (also referred to as a compressed) chewing gum.
  • the presence of natural resins ensures several important features when dealing with granule mixtures for chewing gum, such as improved stickiness of the final chewing gum tablet, improved robustness to softeners, flavors or other relevant chewing gum additives.
  • the balancing between the synthetic and the natural resins ensures that the available gum base may in fact be granulated e.g. by milling without or with reduced risk of sticking to processing equipment.
  • a simplified process may be obtained due to the fact that milling of the gum base granules may optionally be completely avoided e.g. by applying a high-speed mixer, e.g. a Lipp Mixer.
  • the choice of elastomer plasticizers i.e. natural or synthetic resins, will vary depending on the specific application, and on the type of elastomer(s) being used.
  • said natural resin comprises one or more different natural resins.
  • the nature of the different natural resins may typically vary e.g. with respect molecular weight, molecular structure and/or origin.
  • said synthetic resin comprises one or more different synthetic resins.
  • the nature of the different synthetic resins may typically vary e.g. with respect to molecular weight.
  • a combination of for example a low molecular weight and a high molecular weight synthetic resin, e.g. PVA is typically preferred as the synthetic resin forming part of the gum base formulation.
  • the ratio between the synthetic resin and the natural resin is from about 0.5 to about 7, preferably from about 0.9 to about 6.0.
  • a natural resin should always be moderated by synthetic resin, so that the amount of synthetic resin is always at least half the amount of the natural resin present in the gum base and at most in an amount of not more than seven times the amount of natural resins.
  • the ratio between the synthetic resin and the natural resin is from about 0.9 to about 2.0, preferably from about 0.9 to about 1.5.
  • a natural resin should always be moderated by synthetic resin, so that the amount of synthetic resin is always at least about 0.9 of the amount of the natural resin present in the gum base and not more than two times the amount of natural resin in the gum base.
  • the natural resin should, when applied in relatively large amounts, e.g. about 15 to 35% of the gum base be counteracted or supplemented by an about one-to-one relationship with the synthetic resin of the gum base.
  • said natural resin comprises rosin esters.
  • said natural resin comprises terpene resins, e.g. derived from alpha-pinene, beta-pinene, and/or d-limonene, natural terpene resins, glycerol esters of gum rosins, tall oil rosins, wood rosins or other derivatives thereof such as glycerol esters of partially hydrogenated rosins, glycerol esters of polymerized rosins, glycerol esters of partially dimerised rosins, pentaerythritol esters of partially hydrogenated rosins, methyl esters of rosins, partially hydrogenated methyl esters of rosins or pentaerythritol esters of rosins and combinations thereof.
  • terpene resins e.g. derived from alpha-pinene, beta-pinene, and/or d-limonene
  • natural terpene resins e.g. derived from alpha
  • said synthetic resin comprises polyvinyl acetate, vinyl acetate- vinyl laurate copolymers and mixtures thereof.
  • polyvinyl acetate may for example have a GPC average molecular weight in the range of 1,000 to about 90,000, such as the range of 3,000 to 80,000 Mn including the range of 30,000 to 50,000.
  • the vinyl acetate- vinyl laurate copolymers e.g. having a vinyl laurate content of about 5 to about 50% by weight, such as 10 to 45% by weight of the copolymer.
  • said granulated gum base comprising at least one high molecular weight elastomer in an amount of about 0% to about 15% by weight of said gum base, preferably in an amount of about 3% to about 15% by weight of said gum base.
  • the molecular weight of said at least one high molecular weight elastomer is from about 50000 g/mol to 800000 g/mol Mn.
  • said granulated gum base comprising at least one low molecular weight elastomer is in an amount of about 0% to about 25% by weight of said gum base.
  • the molecular weight of said at least one low molecular weight elastomer is from about 1000 g/mol to 50000 g/mol Mn.
  • said gum base has been added lubricants, anti- adherents and glidants such as metallic stearates, hydrogenated vegetable oils, partially hydrogenated vegetable oils, polyethylene glycols, polyoxyethylene monostearates, animal fats, silicates, silicates dioxide, talc, magnesium stearates, calcium stearates, fumed silica, powdered hydrogenated cottonseed oils, hydrogenated vegetable oils, hydrogenated soya oil and mixtures thereof.
  • lubricants such as metallic stearates, hydrogenated vegetable oils, partially hydrogenated vegetable oils, polyethylene glycols, polyoxyethylene monostearates, animal fats, silicates, silicates dioxide, talc, magnesium stearates, calcium stearates, fumed silica, powdered hydrogenated cottonseed oils, hydrogenated vegetable oils, hydrogenated soya oil and mixtures thereof.
  • the gum base is added lubricants, anti-adherents and glidants in an amount as small as possible thereby avoiding reduced texture properties.
  • the gum base is substantially free of lubricants, anti-adherents and glidants.
  • the gum base is substantially free of lubricants, anti-adherents and glidants, thereby obtaining as much texture- improvement as possible by means of the applied combination of synthetic and natural resins.
  • the natural resins provide an improved and sticky texture of the gum base when applied in chewing gum formulation.
  • said gum base is substantially wax free.
  • a substantially wax-free gum base formulation has been obtained having advantageous texture properties when the gum base formulation is moderated with respect to the balance between the synthetic and the natural resins.
  • said gum base is substantially fat free.
  • a substantially fat-free chewing gum formulation benefits for example from improved healthiness.
  • the gum base has a water content of less than 2.0%, preferably less than 1.5% by weight of the gum base.
  • said gum base comprises filler in an amount of about 0% to about 50% by weight of the gum base.
  • said gum base comprises synthetic resin in an amount of about 15% to about 40% by weight of the gum base.
  • a relatively high amount of natural resin e.g. 20% by weight of the gum base
  • An example of such an application would be a ratio of about 1-to-l, whereas reduced content of natural resin advantageously may result in an increased ratio.
  • said gum base comprises emulsif ⁇ ers and/or fats in an amount of about 10% to about 40% by weight of the gum base.
  • said gum base comprises wax in an amount of about 2% to about 30% by weight of the gum base.
  • At least a part of the flavoring agents has been teared into at least a part of the gum base previous to compression.
  • such tearing or incorporation of flavor into the gum base or at least a part of the gum base may e.g. imply mixing of gum base components mechanically during addition of flavor components.
  • the invention relates to a compressed chewing gum comprising elastomer in the amount of about 0.3% to 32% by weight, preferably about 5% to 25% by weight of the chewing gum,
  • said resin comprises
  • the percent by weight measure in relation to the chewing gum refers to the complete chewing gum, except any optional coating.
  • a compressed chewing gum has been made by means of compression of gum base granules and chewing gum additives.
  • the processing abilities of chewing gum base for the purpose of providing a tableted compressed chewing gum is obtained by the providing of a gum base which by nature, i.e. due to the composition, has improved properties with respect to e.g. granulation or other similar pre-processing.
  • natural resins may in fact be used actively for the purpose of moderating the tackiness between two opposing limits, i.e. a lower limit defined by the minimum desired tackiness of the chewing gum and an upper limit defined by the process according to which the chewing gum is made.
  • the desired tackiness may be obtained by applying both natural and synthetic resins in the granulate gum base and by adjusting the mutual balance between the applied amounts of natural and synthetic resins.
  • said chewing gum additives comprises sweeteners in the amount of about 5 to about 95% by weight of the chewing gum, more typically about 20 to about 80% by weight, such as 30 to 60% by weight of the chewing gum.
  • the compressed chewing gum tablet comprises about 0.1% to 15% by weight of flavoring agents, preferably about 0.8% to 5% by weight.
  • said natural resin comprises one or more different natural resins.
  • the nature of the different natural resins may typically vary e.g. with respect to molecular weight, molecular structure and/or origin.
  • said synthetic resin comprises one or more different synthetic resins.
  • the nature of the different synthetic resins may typically vary e.g. with respect to molecular weight.
  • a combination of for example a low molecular weight and a high molecular weight synthetic resin, e.g. PVA is typically preferred as the synthetic resin forming part of the gum base formulation.
  • the ratio between the synthetic resin and the natural resin is from about 0.5 to about 7, preferably from about 0.9 to about 6.0.
  • a natural resin should always be moderated by synthetic resin, so that the amount of synthetic resin is always at least half the amount of the natural resin present in the gum base and at most in an amount of not more than seven times the amount of natural resins.
  • the ratio between the synthetic resin and the natural resin is from about 0.9 to about 2.0, preferably from about 0.9 to about 1.5.
  • a natural resin should always be moderated by synthetic resin, so that the amount of synthetic resin is always at least about 0.9 of the amount of the natural resin present in the gum base and not more than two times the amount of natural resins in the gum base.
  • the natural resin should, when applied in relatively large amounts, e.g. about 15 to 35% of the gum base, be counteracted or supplemented by an about one-to-one relationship with the synthetic resins of the gum base.
  • said natural resin comprises rosin esters.
  • said natural resin comprises terpene resins, e.g. derived from alpha-pinene, beta-pinene, and/or d-limonene, natural terpene resins, glycerol esters of gum rosins, tall oil rosins, wood rosins or other derivatives thereof such as glycerol esters of partially hydrogenated rosins, glycerol esters of polymerized rosins, glycerol esters of partially dimerised rosins, pentaerythritol esters of partially hydrogenated rosins, methyl esters of rosins, partially hydrogenated methyl esters of rosins or pentaerythritol esters of rosins and combinations thereof.
  • terpene resins e.g. derived from alpha-pinene, beta-pinene, and/or d-limonene
  • natural terpene resins e.g. derived from alpha
  • said synthetic resin comprises polyvinyl acetate, vinyl acetate- vinyl laurate copolymers and mixtures thereof.
  • polyvinyl acetate may for example have a GPC average molecular weight in the range of 1,000 to about 90,000, such as the range of 3,000 to 80,000 Mn including the range of 30,000 to 50,000.
  • the vinyl acetate-vinyl laurate copolymers e.g. having a vinyl laurate content of about 5 to about 50% by weight, such as 10 to 45% by weight of the copolymer.
  • said chewing gum comprising at least one high molecular weight elastomer in an amount of about 0% to about 14% by weight of said chewing gum, preferably about 0.5% to about 10% by weight of said chewing gum .
  • the molecular weight of said at least one high molecular weight elastomer is from about 50000 g/mol to 800000 g/mol Mn.
  • said chewing gum comprising at least one low molecular weight elastomer is in an amount of about 0% to about 20% by weight of said chewing gum.
  • the molecular weight of said at least one low molecular weight elastomer is from about 1000 g/mol to 50000 g/mol Mn.
  • said chewing gum comprises lubricants, anti- adherents and glidants such as metallic stearates, hydrogenated vegetable oils, partially hydrogenated vegetable oils, polyethylene glycols, polyoxyethylene monostearates, animal fats, silicates, silicates dioxide, talc, magnesium stearates, calcium stearates, fumed silica, powdered hydrogenated cottonseed oils, hydrogenated vegetable oils, hydrogenated soya oil and mixtures thereof.
  • lubricants such as metallic stearates, hydrogenated vegetable oils, partially hydrogenated vegetable oils, polyethylene glycols, polyoxyethylene monostearates, animal fats, silicates, silicates dioxide, talc, magnesium stearates, calcium stearates, fumed silica, powdered hydrogenated cottonseed oils, hydrogenated vegetable oils, hydrogenated soya oil and mixtures thereof.
  • the chewing gum comprises lubricants, anti-adherents and glidants in an amount as small as possible thereby avoiding reduced texture properties.
  • the chewing gum is substantially free of lubricants, anti-adherents and glidants.
  • the chewing gum is substantially free of lubricants, anti-adherents and glidants, thereby obtaining as much texture-improvement as possible by means of the applied combination of synthetic and natural resins.
  • the natural resins provide an improved and sticky texture of the chewing gum when applied in chewing gum formulation.
  • said chewing gum is substantially wax free.
  • a substantially wax-free chewing gum formulation has been obtained having advantageous texture properties when the chewing gum formulation is moderated with respect to the balance between the synthetic and the natural resins.
  • said chewing gum is substantially fat free.
  • a substantially fat-free chewing gum formulation benefits for example from improved healthiness.
  • the chewing gum has a water content of less than 2.0%, preferably less than 1.5% by weight of the chewing gum.
  • said chewing gum comprises filler in an amount of about 0% to about 50% by weight of the chewing gum.
  • said chewing gum comprises synthetic resin in an amount of about 1.5% to about 35% by weight of the chewing gum.
  • a relatively high amount of natural resin e.g. 20% by weight of the gum base, would typically result in a somewhat reduced use of synthetic resin.
  • An example of such an application would be a ratio of about 1-to-l, whereas reduced content of natural resin advantageously may result in an increased ratio.
  • said chewing gum comprises emulsifiers and/or fats in an amount of about 0.1% to about 35% by weight of the chewing gum.
  • said chewing gum comprises wax in an amount of about 0.5 to about 30% by weight of the chewing gum.
  • At least a part of the flavoring agents has been teared into the chewing gum forming gum base granules or part of the gum base granules previous to compression.
  • said chewing gum additives comprise active ingredients.
  • At least a part of said active ingredients has been teared into the chewing gum or at least a part of the chewing gum previous to compression.
  • the invention relates to a compressed chewing gum tablet comprising gum base according to any of the claims 1-24 in an amount of about 10% to 90% by weight of the chewing gum tablet.
  • the invention also facilitates the providing of a compressed chewing gum tablet comprising a chewing gum center fully or partly encapsulated by a barrier layer, said gum center comprising a compression of gum base granules and chewing gum additives, said gum base granules having a moderated tackiness.
  • Gum base additives may, according to the invention, broadly refer to sweeteners, flavors, acids, colors, active ingredients, cooling agents, freeze-dried fruit, etc. Moreover, the applied ingredients may be encapsulated.
  • additives may be added to the gum base, e.g. during mixing or after mixing.
  • the natural resin facilitates an advantageous overall flavor release when the compressed chewing gum tablet is chewed. This may partly be due to the fact that the initial chewing of the gum tablet results in an immediate release of flavor particles and at the same time that a part of the dissolved flavor particles reacts or become incorporated into the chewing gum base.
  • the last part of the flavor release results in prolonging of the overall flavor release time.
  • a further advantage of the chewing gum tablet according to the invention is that the tablet may be handled and temporarily stored prior to the final processing such as coating and the final packaging.
  • the upper limit of the desired tackiness is reached, when the gum base granules can no longer be processed by conventional compression techniques.
  • the natural resin facilitates an advantageous overall flavor release when the compressed chewing gum tablet is chewed. This may partly be due to the fact that the initial chewing of the gum tablet results in an immediate release of distinct flavor particle and at the same time, that a part of the dissolved flavor particles reacts or become incorporated into the chewing gum base.
  • the natural resins as provided and balanced with respect synthetic resins according to the invention has shown advantageous release properties compared to e.g. chewing gums comprising synthetic resins only.
  • the "% by weight" of the chewing gum tablet refers to the un-coated chewing gum tablet.
  • the compressed chewing gum tablet comprises about 0.1% to 15% by weight of flavoring agents, preferably about 0.8% to 5% by weight, a further advantageous embodiment of the invention has been obtained.
  • the amount of flavor depends heavily of the applied type of flavor and whether the flavor has been partly teared into the gum base or part of the gum base previous to the compression of the gum base granules and the chewing gum additives.
  • the natural resins provide an improved and sticky texture of the tablet, a further advantageous embodiment of the invention has been obtained.
  • natural resins provide an improved and sticky texture of the final compressed tablet compared to traditional compressed chewing gum.
  • the desired moderated tackiness may in certain compositions be "tuned” by means of the wax content, which, when applied in an increased amount in the context of certain gum base compounds, may increase the tackiness of the final barrier- encapsulated composition.
  • adjustment of the desired initial tackiness may be performed without wax.
  • a controlled release of active ingredients may be obtained by means of at least a double active ingredients buffer, the first buffer comprising active ingredients blended into the final mix immediately prior to compression, the second buffer comprising active ingredients blended into the gum base prior to the blending of gum base and chewing gum base additives.
  • fig- 1 illustrates a chewing gum tablet according to the invention
  • fig. 2a and 2b illustrate flowcharts of two applicable alternative manufacturing methods according to examples of embodiments of the invention
  • fig- 3 illustrates the compression of a chewing gum according to one embodiment of the invention
  • fifigg.. 4 4 illustrates the compression of a chewing gum according to another embodiment of the invention.
  • Fig. 1 illustrates a chewing gum tablet according to the invention.
  • the fig. 1 illustrates a chewing gum tablet made on the basis of compressed gum base granulates.
  • the gum tablet comprises a barrier layer 1 encapsulating or partly encapsulating a gum base center 2.
  • the gum base granulates are made on the basis of a gum base.
  • the expression "gum base” refers in general to the water insoluble part of the chewing gum, which typically constitutes 10 to 90% by weight including the range of 15-50% by weight of the total chewing gum formulation.
  • Chewing gum base formulations typically comprise one or more elastomeric compounds of synthetic or natural origin, at least two resinous compounds which, according to the invention is both of synthetic or natural origin, fillers, softening compounds and minor amounts of miscellaneous ingredients such as antioxidants and colorants, etc.
  • the gum base should always comprise at least an amount of 5% by weight of natural resins and less than about 40% by weight of the gum base and the synthetic resin should be present in an amount of about 15% to about 40% by weight of the gum base.
  • composition of chewing gum base formulations mixed with chewing gum additives can vary substantially depending on the particular product to be prepared and on the desired masticatory and other sensory characteristics of the final product.
  • typical ranges (weight%) of the above gum base components are: 5 to 50% by weight elastomeric compounds, 5 to 55% by weight resins, 0 to 50% by weight filler/texturiser, 5 to 35% by weight softener and 0 to 1% by weight of miscellaneous ingredients such as antioxidants, colorants, etc.
  • the barrier layer 1 may preferably be applied during or prior to the processing of the tablet.
  • the barrier layer e.g. Mg Stearate, forms an outer barrier of the gum tablet.
  • Fig. 2a shows a typical flowchart, illustrating the major steps of one of several applicable manufacturing processes within the scope of the invention.
  • step 21 a suitable gum base is prepared according to the prescriptions of the invention.
  • the gum base is partly pre- mixed with a moderated amount of flavor and/or active ingredients.
  • the pre-mixing of flavors or active ingredients may e.g. be performed by means of conventional mixers, e.g. a Z-blade mixer, during no or preferably relatively little added heating and substantially under atmospheric pressure.
  • the pre- mixing also referred to a tearing
  • Typical duration in time of mixing may be between few minutes op to e.g. 30 minutes.
  • other temperatures, pressures, duration in time and mixing methods may be applied for the purpose of mixing active ingredients and/or flavors into the gum base and thereby the gum base granulate applied for the subsequent compression.
  • the provided gum base is grinding (by some referred to as granulated).
  • the granulating may be performed by means of well-known techniques. One of those techniques implies an initial cooling of the gum base immediately prior to granulation. If the consistence of the gum base allows so, the provided gum base may be granulated at room temperature.
  • bulk-sweeteners may advantageously be applied as a grinding aid. Sorbitol can be used as a non-sugar sweetener.
  • Non-sugar sweeteners include, but are not limited to, other sugar alcohols such as mannitol, xylitol, hydrogenated starch hydrolysates, maltitol, isomaltol, erythritol, lactitol and the like, alone or in combination.
  • sugar alcohols such as mannitol, xylitol, hydrogenated starch hydrolysates, maltitol, isomaltol, erythritol, lactitol and the like, alone or in combination.
  • step 23 the gum base granulate is blended with suitable chewing gum additives.
  • chewing gum additives include bulk sweeteners, high- intensity sweeteners, flavoring agents, softeners, emulsifiers, coloring agents, binding agents, acidulants, fillers, antioxidants and other components such as pharmaceutically or biologically active substances, that confer desired properties to the finished chewing gum product.
  • Suitable bulk sweeteners include e.g. both sugar and non-sugar components.
  • Bulk sweeteners typically constitute from about 5 to about 95% by weight of the chewing gum, more typically about 20 to about 80% by weight such as 30 to 60% by weight of the gum.
  • Useful sugar sweeteners are saccharide-containing components commonly known in the chewing gum art including, but not limited to, sucrose, dextrose, maltose, dextrins, trehalose, D-tagatose, dried invert sugar, fructose, levulose, galactose, corn syrup solids, and the like, alone or in combination.
  • Sorbitol can be used as a non-sugar sweetener.
  • Other useful non-sugar sweeteners include, but are not limited to, other sugar alcohols such as mannitol, xylitol, hydrogenated starch hydrolysates, maltitol, isomaltol, erythritol, lactitol and the like, alone or in combination.
  • High-intensity artificial sweetening agents can also be used alone or in combination with the above sweeteners.
  • Preferred high-intensity sweeteners include, but are not limited to, sucralose, aspartame, salts of acesulfame, alitame, saccharin and its salts, neotam, cyclamic acid and its salts, glycyrrhizin, dihydrochalcones, thaumatin, monellin, sterioside and the like, alone or in combination.
  • it may be desirable to encapsulate or otherwise control the release of at least a portion of the artificial sweetener. Techniques such as wet granulation, wax granulation, spray drying, spray chilling, fluid bed coating, coascervation, encapsulation in yeast cells and fiber extrusion may be used to achieve desired release characteristics.
  • usage level of the artificial sweetener will vary considerably depending e.g. on factors such as potency of the sweetener, rate of release, desired sweetness of the product, level and type of flavor used and cost considerations.
  • the active level of artificial sweetener may vary from about 0.02 to about 8% by weight.
  • the usage level of the encapsulated sweetener will be proportionately higher.
  • Combinations of sugar and/or non-sugar sweeteners can be used in the chewing gum formulation processed in accordance with the invention. Additionally, the softener may also provide additional sweetness such as with aqueous sugar or alditol solutions.
  • a low-calorie bulking agent can be used.
  • low-calorie bulking agents include polydextrose, Raftilose, Raftilin, friuline, fructooligosaccharides (NutraFlora ® ), palatinose oligosaccharided; guar gum hydrolysates (e.g. Sun Fiber ® ) or indigestible dextrins (e.g. Fibersol ® ).
  • other low-calorie bulking agents can be used.
  • compositions which may be included in the chewing gum mixture processed in the present process include surfactants and/or solubilisers, especially when pharmaceutically, cosmetically or biologically active ingredients are present.
  • surfactants As examples of types of surfactants to be used as solubilisers in a chewing gum composition according to the invention reference is made to H.P. Fiedler, Lexikon der Hilfstoffe fur Pharmacie, Kosmetik und Angrenzende füre, page 63-64 (1981) and the lists of approved food emulsifiers of the individual countries.
  • Anionic, cationic, amphoteric or non-ionic solubilisers can be used.
  • Suitable solubilisers include lecithins, polyoxyethylene stearate, polyoxyethylene sorbitan fatty acid esters, fatty acid salts, mono and diacetyl tartaric acid esters of mono and diglycerides of edible fatty acids, citric acid esters of mono and diglycerides of edible fatty acids, saccharose esters of fatty acids, polyglycerol esters of fatty acids, polyglycerol esters of interesterified castor oil acid (E476), sodium stearoyllatylate, sodium lauryl sulfate and sorbitan esters of fatty acids and polyoxyethylated hy- drogenated castor oil (e.g.
  • CREMOPHOR block copolymers of ethylene oxide and propylene oxide (e.g. products sold under trade names PLURONIC and POLOXAMER), polyoxyethylene fatty alcohol ethers, polyoxyethylene sorbitan fatty acid esters, sorbitan esters of fatty acids and polyoxyethylene steraric acid esters.
  • solubilisers are polyoxyethylene stearates, such as for instance polyoxyethylene(8)stearate and polyoxyethylene(40)stearate, the polyoxyethylene sorbitan fatty acid esters sold under the trade name TWEEN, for instance TWEEN 20 (monolaurate), TWEEN 80 (monooleate), TWEEN 40 (monopalmitate), TWEEN 60 (monostearate) or TWEEN 65 (tristearate), mono and diacetyl tartaric acid esters of mono and diglycerides of edible fatty acids, citric acid esters of mono and diglycerides of edible fatty acids, sodium stearoyllactylate, sodium laurylsulfate, polyoxyethylated hydrogenated castor oil, blockcopolymers of ethylene oxide and propyleneoxide and polyoxyethylene fatty alcohol ether.
  • the solubiliser may either be a single compound or a combination of several compounds.
  • solubiliser is used in the present text to describe both possibilities, the solubiliser used must be suitable for use in food and/or medicine.
  • the chewing gum may preferably also comprise a carrier known in the art.
  • a carrier known in the art.
  • One significant advantage of the present process is that the temperature throughout the entire operation can be kept at a relatively low level such as it will be described in the following. This is an advantageous feature with regard to preserving the aroma of added flavoring components, which may be prone to deterioration at higher temperatures.
  • Aroma agents and flavoring agents which are useful in a chewing gum produced by the present process are e.g. natural and synthetic flavorings (including natural flavorings) in the form of freeze-dried natural vegetable components, essential oils, essences, extracts, powders, including acids and other substances capable of affecting the taste profile.
  • liquid and powdered flavorings include coconut, coffee, chocolate, vanilla, grape fruit, orange, lime, menthol, liquorice, caramel aroma, honey aroma, peanut, walnut, cashew, hazelnut, almonds, pineapple, strawberry, raspberry, tropical fruits, cherries, cinnamon, peppermint, wintergreen, spearmint, eucalyptus, and mint, fruit essence such as from apple, pear, peach, strawberry, apricot, raspberry, cherry, pineapple, and plum essence.
  • the essential oils include peppermint, spearmint, menthol, eucalyptus, clove oil, bay oil, anise, thyme, cedar leaf oil, nutmeg, and oils of the fruits mentioned above.
  • the flavor is one or more natural flavoring agent(s) which is/are freeze-dried, preferably in the form of a powder, slices or pieces or combinations thereof.
  • the particle size of such agents may be less than 3 mm, such as less than 2 mm, more preferred less than 1 mm, calculated as the longest dimension of the particle.
  • the natural flavoring agent may also be in a form where the particle size is from about 3 ⁇ m to 2 mm, such as from 4 ⁇ m to 1 mm.
  • Preferred natural flavoring agents include seeds from a fruit e.g. from strawberry, blackberry and raspberry.
  • the aroma agent may be used in quantities smaller than those conventionally used.
  • the aroma agents and/or flavors may be used in an amount of about 0.01 to about 30% by weight of the final product depending on the desired intensity of the aroma and/or flavor used.
  • the content of aroma/flavor is in the range of about 0.2 to 3% by weight of the total composition.
  • encapsulated flavors or active ingredients may be added to the final blend, e.g. in step 23 of fig. 2, prior to compression.
  • flavors or active ingredients which may both refer to flavors or active ingredients mixed into the gum base and flavors or active ingredients compressed into the chewing gum may e.g. include Spray drying, Spray cooling, Film coating, Coascervation, Double emulsion method (Extrusion technology) or Prilling.
  • Materials to be used for the above-mentioned encapsulation methods may e.g. include Gelatine, Wheat protein, Soya protein, Sodium caseinate, Caseine, Gum arabic, Mod. starch, Hydrolyzed starches (maltodextrines), Alginates, Pectin, Carregeenan, Xanthan gum, Locus bean gum, Chitosan, Bees wax, Candelilla wax, Carnauba wax, Hydrogenated vegetable oils, Zein and/or Sucrose.
  • Gelatine Wheat protein, Soya protein, Sodium caseinate, Caseine, Gum arabic, Mod. starch, Hydrolyzed starches (maltodextrines), Alginates, Pectin, Carregeenan, Xanthan gum, Locus bean gum, Chitosan, Bees wax, Candelilla wax, Carnauba wax, Hydrogenated vegetable oils, Zein and/or Sucrose.
  • Active ingredients may be added to chewing gum. Preferably, these ingredients should be added subsequent to any significant heating or mixing. In other words, the active ingredients, should preferably be added immediately prior to the compression of the final tablet.
  • the adding of active ingredients may be cautiously blended with pre-mixed gum base granulates and further desired additives, immediately prior to the final compression of the tablet.
  • the chewing gum comprises a pharmaceutically, cosmetically or biologically active substance.
  • active substances include drugs, dietary supplements, antiseptic agents, pH- adjusting agents, anti-smoking agents and substances for the care or treatment of the oral cavity and the teeth such as hydrogen peroxide and compounds capable of releasing urea during chewing.
  • useful active substances in the form of antiseptics include salts and derivatives of guanidine and biguanidine (for instance chlorhexidine diacetate) and the following types of substances with limited water- solubility: quaternary ammonium compounds (e.g.
  • ceramine chloroxylenol, crystal violet, chloramine
  • aldehydes e.g. paraformaldehyde
  • derivatives of dequaline polynoxyline
  • phenols e.g. thymol, p-chlorophenol, cresol
  • hexachlorophene salicylic anilide compounds
  • triclosan halogenes (iodine, iodophores, chloroamine, dichlorocyanuric acid salts)
  • alcohols (3,4 dichlorobenzyl alcohol, benzyl alcohol, phenoxyethanol, phenylethanol), cf.
  • metal salts, complexes and compounds with limited water- solubility such as aluminum salts, (for instance aluminum potassium sulphate AlK(SO ) 2 ,12H 2 O) and salts, complexes and compounds of boron, barium, strontium, iron, calcium, zinc, (zinc acetate, zinc chloride, zinc gluconate), copper (copper chloride, copper sulphate), lead, silver, magnesium, sodium, potassium, lithium, molybdenum, vanadium should be included; other compositions for the care of mouth and teeth: for instance; salts, complexes and compounds containing fluorine (such as sodium fluoride, sodium monofluorophosphate, aminofluorides, stannous fluoride), phosphates, carbonates and selenium. Further active substances can be found in J. Dent.Res. Vol. 28 No. 2, page 160-171,1949.
  • active substances in the form of agents adjusting the pH in the oral cavity include: acids, such as adipinic acid, succinic acid, fumaric acid, or salts thereof or salts of citric acid, tartaric acid, malic acid, acetic acid, lactic acid, phosphoric acid and glutaric acid and acceptable bases, such as carbonates, hydrogen carbonates, phosphates, sulphates or oxides of sodium, potassium, ammonium, magnesium or calcium, especially magnesium and calcium.
  • acids such as adipinic acid, succinic acid, fumaric acid, or salts thereof or salts of citric acid, tartaric acid, malic acid, acetic acid, lactic acid, phosphoric acid and glutaric acid and acceptable bases, such as carbonates, hydrogen carbonates, phosphates, sulphates or oxides of sodium, potassium, ammonium, magnesium or calcium, especially magnesium and calcium.
  • Active ingredients may comprise the below-mentioned compounds or derivates thereof but are not limited thereto: Acetaminophen, Acetylsalicylsyre Bupreno ⁇ hine
  • Chloride Benzeth. Chloride, Cetylpyrid. Chlorhexidine, Ecabet-sodium, Haloperidol, Allopurinol, Colchinine, Theophylline, Propanolol, Prednisolone, Prednisone, Fluoride, Urea, Actot, Glibenclamide, Glipizide, Metformin, Miglitol, Repaglinide, Rosiglitazone, Apomorfin, Cialis, Sildenafil, Vardenafil, Diphenoxylate, Simethicone, Cimetidine, Famotidine, Ranitidine, Ratinidine, cetrizin, Loratadine, Aspirin, Benzocaine, Dextrometo ⁇ han, Phenylpropanolamine, Pseudoephedrine, Cisapride, Domperidone, Metoclopramide, Acyclovir, Dioctylsulfosucc, Phenolph
  • the invention is suitable for increased or accelerated release of active agents selected among the group of dietary supplements, oral and dental compositions, antiseptic agents, pH-adjusting agents, anti-smoking agents, sweeteners, flavorings, aroma agents or drugs. Some of those will be described below.
  • the active agents to be used in connection with the present invention may be any substance desired to be released from the chewing gum.
  • the active agents, for which a controlled and/or accelerated rate of release is desired are primarily substances with a limited water-solubility, typically below 10 g/100 ml inclusive of substances which are totally water-insoluble. Examples are medicines, dietary supplements, oral compositions, anti-smoking agents, highly potent sweeteners, pH-adjusting agents, flavorings, etc.
  • active ingredients are, for instance, paracetamol, benzocaine, cinnarizine, menthol, carvone, caffeine, chlorhexidine-di-acetate, cyclizine hydrochloride, 1,8- cineol, nandrolone, miconazole, mystatine, aspartame, sodium fluoride, nicotine, saccharin, cetylpyridinium chloride, other quaternary ammoniumcompounds, vitamin E, vitamin A, vitamin D, glibenclamide or derivatives thereof, progesterone, acetyl- salicylic acid, dimenhydrinate, cyclizine, metronidazole, sodium hydrogencarbonate, the active components from ginkgo, the active components from propolis, the active components from ginseng, methadone, oil of peppermint, salicylamide, hydrocortisone or astemizole.
  • active agents in the form of dietary supplements are for instance salts and compounds having the nutritive effect of vitamin B2 (riboflavin), B12, Folic acid, niacine, biotine, poorly-soluble glycerophosphates, amino acids, the vitamins A, D, E and K, minerals in the form of salts, complexes and compounds containing calcium, phosphorus, magnesium, iron, zinc, copper, iodine, manganese, chromium, selenium, molybdenum, potassium, sodium or cobalt.
  • vitamin B2 riboflavin
  • B12 riboflavin
  • Folic acid niacine
  • biotine poorly-soluble glycerophosphates
  • amino acids amino acids
  • the vitamins A, D, E and K minerals in the form of salts, complexes and compounds containing calcium, phosphorus, magnesium, iron, zinc, copper, iodine, manganese, chromium, selenium, molybdenum, potassium, sodium or
  • active agents in the form of compounds for the care or treatment of the oral cavity and the teeth are for instance bound hydrogen peroxide and compounds capable of releasing urea during chewing.
  • active agents in the form of antiseptics are for instance salts and compounds of guanidine and biguanidine (for instance chlorhexidine diacetate) and the following types of substances with limited water-solubility: quaternary ammonium compounds (for instance ceramine, chloroxylenol, crystal violet, chloramine), aldehydes (for instance paraformaldehyde), compounds of dequaline, polynoxyline, phenols (for instance thymol, para chlorophenol, cresol) hexachlorophene, salicylic anilide compounds, triclosan, halogenes (iodine, iodo- phores, chloroamine, dichlorocyanuric acid salts), alcohols (3,4 dichlorobenzyl alcohol, benzyl alcohol, phenoxyethanol,
  • metal salts, complexes and compounds with limited water-solubility such as aluminum salts, (for instance aluminum potassium sulfate AlK(SO 4 ) 2 ,12H 2 O) and furthermore salts, complexes and compounds of boron, barium, strontium, iron, calcium, zinc, (zinc acetate, zinc chloride, zinc gluconate), copper (copper chloride, copper sulfate), lead, silver, magnesium, sodium, potassium, lithium, molybdenum, vanadium should be included; other compositions for the care of mouth and teeth: for instance; salts, complexes and compounds containing fluorine (such as sodium fluoride, sodiummono- fluorophosphate, aminofluorides, stannous fluoride), phosphates, carbonates and selenium.
  • fluorine such as sodium fluoride, sodiummono- fluorophosphate, aminofluorides, stannous fluoride
  • active agents in the form of agents adjusting the pH in the oral cavity include for instance: acceptable acids, such as adipinic acid, succinic acid, fumaric acid, or salts thereof or salts of citric acid, tartaric acid, malic acid, acetic acid, lactic acid, phosphoric acid and glutaric acid and acceptable bases, such as carbonates, hydrogen carbonates, phosphates, sulfates or oxides of sodium, potassium, ammonium, magnesium or calcium, especially magnesium and calcium.
  • acceptable acids such as adipinic acid, succinic acid, fumaric acid, or salts thereof or salts of citric acid, tartaric acid, malic acid, acetic acid, lactic acid, phosphoric acid and glutaric acid and acceptable bases, such as carbonates, hydrogen carbonates, phosphates, sulfates or oxides of sodium, potassium, ammonium, magnesium or calcium, especially magnesium and calcium.
  • active agents in the form of anti-smoking agents include for instance: nicotine, tobacco powder or
  • sucrose fatty acid esters may also be utilized for increased release of sweeteners including for instance the so-called highly potent sweeteners, such as for instance saccharin, cyclamate, aspartame, thaumatin, dihydrocalcones, stevioside, glycyrrhizin or salts or compounds thereof.
  • highly potent sweeteners such as for instance saccharin, cyclamate, aspartame, thaumatin, dihydrocalcones, stevioside, glycyrrhizin or salts or compounds thereof.
  • the sucrose fatty acids preferably have a content of palmitate of at least 40% such as at least 50%.
  • active agents are medicines of any type.
  • active agents in the form of medicines include caffeine, salicylic acid, salicyl amide and related substances (acetylsalicylic acid, choline salicylate, magnesium salicylate, sodium salicylate), paracetamol, salts of pentazocine (pentazocine hydrochloride and pentazocinelactate), bupreno ⁇ hine hydrochloride, codeine hydro- chloride and codeine phosphate, mo ⁇ hine and mo ⁇ hine salts (hydrochloride, sulfate, tartrate), methadone hydrochloride, ketobemidone and salts of ketobemidone (hydrochloride), beta-blockers, (propranolol), calcium antagonists, verapamil hydrochloride, nifedinpine as well as suitable substances and salts thereof mentioned in Pharm.
  • glucoseoxidase streptokinase, streptodornase, dextranase, alpha amylase
  • polypeptides oxytocin, gonadorelin, (LH.RH), desmopressin acetate (DDAVP), isoxsuprine hydrochloride, ergotamine compounds, chloroquine (phosphate, sulfate), isosorbide, demoxytocin, heparin.
  • Dental products include Carbamide, CPP Caseine Phospho Peptide; Chlorhexidine, Chlorhexidine di acetate, Chlorhexidine Chloride, Chlorhexidine di gluconate, Hexetedine, Strontium chloride, Potassium Chloride, Sodium bicarbonate, Sodium carbonate, Fluor containing ingredients, Fluorides, Sodium fluoride, Aluminum fluoride, Ammonium fluoride, Calcium fluoride, Stannous fluoride, Other fluor containing ingredients Ammonium fluorosilicate, Potasium fluorosilicate, Sodium fluorosilicate, Ammonium monofluo ⁇ hosphate, Calcium monofluo ⁇ hosphate, Potassium monofluo ⁇ hosphate, Sodium monofluo ⁇ hosphate, Octadecentyl Ammonium fluoride, Stearyl Trihydroxyethyl Propylened
  • Minerals include Calcium, phosphor, magnesium, iron, Zink, Cupper, Iod, Mangan, Crom, Selene, Molybden.
  • Other active ingredients include: Q10 ® , enzymes.
  • Natural drugs including Ginkgo Biloba, ginger, and fish oil.
  • the invention also relates to use of migraine drugs such as Serotonin antagonists: Sumatriptan, Zolmitriptan, Naratriptan, Rizatriptan, Eletriptan; nausea drugs such as Cyclizin, Cinnarizin, Dimenhydramin, Difenhydrinat; hay fever drugs such as Cetrizin, Loratidin, pain relief drugs such as Buprenorfin, Tramadol, oral disease drugs such as Miconazol, Amphotericin B, Triamcinolonaceton; and the drugs Cisaprid, Domperidon, Metoclopramid.
  • Serotonin antagonists Sumatriptan, Zolmitriptan, Naratriptan, Rizatriptan, Eletriptan
  • nausea drugs such as Cyclizin, Cinnarizin, Dimenhydramin, Difenhydrinat
  • hay fever drugs such as Cetrizin, Loratidin
  • pain relief drugs such as Buprenorfin, Tramadol
  • oral disease drugs such
  • the above-mentioned active ingredients and/or flavors may be pre-mixed into the gum base.
  • a controlled release of active ingredients may be obtained by means of at least a double active ingredients buffer, the first buffer comprising active ingredients blended into the final mix immediately prior to compression, the second buffer comprising active ingredients blended into the gum base prior to the blending of gum base and gum base additives.
  • release of flavor and/or active ingredients maybe adjusted by adjustment of the balance between pre-mixed ingredients and the chewing gum additives added prior to compression.
  • step 24 the resulting blend is prepared for tableting by means of sieving.
  • the degree of sieving depends primarily of how the gum base granulate(s) "reacts" when chewing gum additives are blended together.
  • an initial pre-forming of the granulates are supplemented by spraying the barrier layer at the surface or at least a part of the surface of the pre-formed granulates.
  • This technique and variants thereof may be referred to as an explicit barrier layer depositing.
  • the barrier layer is established in a more implicit way.
  • This technique and variants thereof may be referred to as implicit barrier layer depositing. This technique implies that the barrier layer compound is sprayed or deposited initially on the contacting surfaces of the pressing tools of a compression machine.
  • step 25 the grinded blend is applied to the pressing tools of a tableting machine and compressed into chewing gum tablets.
  • the applied barrier layer may comprise of e.g. lubricants, anti-adherents and glidants.
  • Magnesium stearate may e.g. be applied as a pulverized parting compound.
  • the barrier layer may be added to the final tablet for example by depositing dosed quantities of pulverized lubricants and parting compounds on the material contacting surfaces of pressing tools of tableting machines.
  • the barrier layer may be established by means of for example metallic stearates, hydrogenated vegetable oils, partially hydrogenated vegetable oils, polyethylene glycols, polyoxyethylene monostearates, animal fats, silicates, silicates dioxide, talc, magnesium stearates, calcium stearates, fumed silica, powdered hydrogenated cottonseed oils, hydrogenated vegetable oils, hydrogenated soya oil and mixtures thereof.
  • step 26 which is optional, but preferred, the tableted chewing gum is provided with a suitable coating.
  • the chewing gum element comprises about 5% to about 98% by weight of the complete weight of the coated chewing gum.
  • a suitable outer coating is any coating that results in an extended storage stability of the compressed chewing gum products as defined above, relative to a chewing gum of the same composition that is not coated.
  • suitable coating types include hard coatings, film coatings and soft coatings of any composition including those currently used in coating of chewing gum, pharmaceutical products and confectioneries.
  • film coating is applied to the compressed chewing gum tablet.
  • One presently preferred outer coating type is a hard coating, which term is used in the conventional meaning of that term including sugar coatings and sugar-free (or sugarless) coatings and combinations thereof.
  • the objects of hard coating are to obtain a sweet, crunchy layer, which is appreciated by the consumer, and to protect the gum centers for various reasons.
  • a typical process of providing the chewing gum centers with a protective sugar coating the gum centers are successively treated in suitable coating equipment with aqueous solutions of crystallizable sugar such as sucrose or dextrose, which, depending on the stage of coating reached, may contain other functional ingredients, e.g. fillers, colors, etc.
  • the sugar coating may contain further functional or active compounds including flavor compounds, pharmaceutically active compounds and/or polymer degrading substances.
  • sorbitol, maltitol, mannitol, xylitol, erythritol, lactitol, isomalt and tagatose which are obtained by industrial methods by hydrogenation of D-glucose, maltose, fructose or levulose, xylose, erythrose, lactose, isomaltulose and D-galactose, respectively.
  • a syrup containing crystallizable sugar and/or polyol is applied onto the gum centers and the water it contains is evaporated off by blowing with warm, dry air. This cycle must be repeated several times, typically 10 to 80 times, in order to reach the swelling required.
  • swelling refers to the increase in weight of the products, as considered at the end of the coating operation by comparison with the beginning, and in relation to the final weight of the coated products.
  • the coating layer constitutes about 1 to about 75% by weight of the finished chewing gum element, such as about 10 to about 60% by weight, including about 15 to about 50% by weight.
  • the outer coating of the chewing gum element is an element that is subjected to a film coating process and which therefore comprises one or more film-forming polymeric agents and optionally one or more auxiliary compounds, e.g. plasticizers, pigments and opacifiers.
  • a film coating is a thin polymer-based coating applied to a chewing gum center of any of the above forms. The thickness of such a coating is usually between 20 and 100 ⁇ m.
  • the film coating is obtained by passing the chewing gum centers through a spray zone with atomized droplets of the coating materials in a suitable aqueous or organic solvent vehicle, after which the material adhering to the gum centers is dried before the next portion of coating is received. This cycle is repeated until the coating is complete.
  • suitable film-coating polymers include edible cellulose derivatives such as cellulose ethers including methylcellulose (MC), hydroxyethyl cellulose (HEC), hydroxypropyl cellulose (HPC) and hydroxypropyl methylcellulose (HPMC).
  • Other useful film-coating agents are acrylic polymers and copolymers, e.g. methylacrylate aminoester copolymer or mixtures of cellulose derivatives and acrylic polymers.
  • a particular group of film-coating polymers also referred to, as functional polymers are polymers that, in addition to its film-forming characteristics, confer a modified release performance with respect to active components of the chewing gum formulation.
  • Such release modifying polymers include methylacrylate ester copolymers, ethylcellulose (EC) and enteric polymers designed to resist the acidic stomach environment, yet dissolve readily in the duodenum.
  • the latter group of polymers includes: cellulose acetate phtalate (CAP), polyvinyl acetate phtalate (PVAP), shellac, metacrylic acid copolymers, cellulose acetate trimellitate (CAT) and HPMC.
  • CAP cellulose acetate phtalate
  • PVAP polyvinyl acetate phtalate
  • shellac metacrylic acid copolymers
  • CAT cellulose acetate trimellitate
  • HPMC cellulose acetate trimellitate
  • the outer film coating according to the present invention may comprise any combination of the above film-coating polymers.
  • the film-coating layer of the chewing gum elements comprise a plasticizing agent having the capacity to alter the physical properties of a polymer to render it more useful in performing its function as a film- forming material.
  • plasticizers will be to make the polymer softer and more pliable as the plasticizer molecules inte ⁇ ose themselves between the individual polymer strands thus breaking down polymer-polymer interactions.
  • plasticizers used in film coating are either amo ⁇ hous or have very little crystallinity.
  • suitable plasticizers include polyols such as glycerol, propylene glycol, polyethylene glycol, e.g.
  • organic esters such as phtalate esters, dibutyl sebacate, citrate esters and thiacetin
  • oils/glycerides including castor oil, acetylated monoglycerides and fractionated coconut oil.
  • film-forming polymer(s) and plasticizing agent(s) for the outer coating of the present chewing gum element is made with due consideration for achieving the best possible barrier properties of the coating in respect of dissolution and diffusion across the film of moisture and gasses.
  • the film coating of the chewing gum elements may also contain one or more colorants or opacifiers.
  • colorants or opacifiers include organic dyes and their lakes, inorganic coloring agents, e.g. titanium oxide and natural colors such as e.g. ⁇ -carotene.
  • film coatings may contain one or several auxiliary substances such as flavors and waxes or saccharide compounds such as polydextrose, dextrins including maltodextrin, lactose, modified starch, a protein such as gelatine or zein, a vegetable gum and any combination thereof.
  • auxiliary substances such as flavors and waxes or saccharide compounds such as polydextrose, dextrins including maltodextrin, lactose, modified starch, a protein such as gelatine or zein, a vegetable gum and any combination thereof.
  • the outer coating of the chewing gum element can contain one or more pharmaceutically or cosmetically components including those mentioned hereinbefore.
  • the above hard-coated or film- coated chewing gum element is an element where the outer coating comprises at least one additive component selected from a binding agent, a moisture absorbing component, a film forming agent, a dispersing agent, an anti-sticking component, a bulking agent, a flavoring agent, a coloring agent, a pharmaceutically or cosmetically active component, a lipid component, a wax component, a sugar and an acid.
  • a binding agent e.g. a protein including gelatine and soy protein, a cellulose derivative including any of those mentioned above, a starch derivative, edible synthetic polymers and lipid substances, the latter optionally in the form of liposome encapsulation.
  • the chewing gum element is provided with an outer coating in the form generally described in the art as a soft coating.
  • a soft coating is applied using conventional methods and may advantageously consist of a mixture of a sugar or any of the above non-cariogenic, sugar-less sweetening compounds, and a starch hydrolysate.
  • the above-described coating is optional or that it may be postponed until it fits into the last part of the manufacturing process due to the fact that the applied barrier layer is also acting as a complete or at least a partial barrier to transfer of humidity from the environment into the tablet.
  • Fig. 2b illustrates a further embodiment of the invention.
  • the illustrated process corresponds to the process illustrated in fig. 2a, although some important process steps have been modified, namely step 21 and the omission of step 22.
  • a blend as provided in step 23 and 24, is injected into the pressing tool 31.
  • the blend comprises gum base granules 32 and gum base additives 33 such as additional sweeteners, additional flavors, etc. Suitable chewing gum additives have been disclosed above.
  • the pressing tools 31 and 35 has been pressed together, thereby invoking a compression of the gum base blending of gum base granules 32 and further chewing gum additives 33.
  • the resulting chewing gum tablet 37 comprises a chewing gum center 38 comprising a compression of the gum base granules 32 and the gum base additives 33.
  • a final barrier layer 39 is formed as a combining of barrier layer LI and barrier layer L2.
  • the - evidently moderated - tackiness of the gum base granules 32 or at least a part of the granules is provided by means of e.g. natural resins inco ⁇ orated in the gum base granulate.
  • Fig. 4a to 4d illustrate a further embodiment of the invention.
  • a blend e.g. as provided according to the processes illustrated in fig. 2a and 2b is injected into the pressing tool 41.
  • the blend comprises gum base granules 42 and gum base additives 43 such as additional sweeteners, additional flavors, etc. Suitable chewing gum additives have been disclosed above.
  • the pressing tools 41 and 45 have been pressed together, thereby invoking a compression of the gum base blending of gum base granules 42 and further chewing gum additives 43.
  • the resulting chewing gum tablet 47 comprises a chewing gum center 48 comprising a compression of the gum base granules 42 and the gum base additives 43.
  • the final tablets of e.g. fig. 3e and 4d may moreover be provided with a coating.
  • the compression of a gum base granulate together with chewing gum additives is a relatively lenient gathering of the final chewing gum, at least with respect to temperature.
  • the omission of the thoroughly tearing of the granulate together with the desired additives will, 39 according to conventional chewing gum, result in a risk of crumbling and disintegration especially during the initial chew.
  • the provided chewing gum featuring tacky granules may counteract the initial-chew invoked disintegration to such a degree that the chewing gum remains non-crumbling until the granules are finally mixed during the chewing of the chewing gum.
  • the last row refers to the amount of natural resin of the complete chewing gum.
  • the provided chewing gum was tested by a sensory panel of 8 persons.
  • Example 1 and 3 were deemed to have an impressing initial chew and moreover an impressing flavor release. Deemed OK.
  • Example 2 was deemed to be OK, but giving a feeling of a little more vulnerable initial chew.
  • Example 4 had an almost liquid consistence, and the obtained chewing gum was deemed not OK.
  • the gum bases were composed as described in the following table:
  • the gum bases are prepared as follows:
  • the elastomers are added to a mixing kettle provided with mixing means like e.g. horizontally placed Z-shaped arms.
  • the elastomers are broken into small pieces and softened with mechanical action on the kettle.
  • the natural resins are slowly added to the elastomers and when the mixture becomes homogeneous the PVA is added.
  • the filler is admixed successively in portions capable of being absorbed into the mixture.
  • the softening system comprising emulsifiers, fats and/or wax is slowly added into the mixture and mixing is continued until a homogenous gum base is obtained.
  • Mixing time is typically in the range of 30 minutes to 4 hours depending of the composition and mixing technology.
  • the mixing temperature will typically be in the range from 50° C to 120° C.
  • the mixture is then discharged into the pan or pelletizied and allowed to cool to room temperature from the discharged temperature of 50-120° C.
  • the compressed chewing gum formulation is as follows.
  • the sensory evaluation of the texture was made with reference to a conventional chewing gum, which is ranked, as excellent.
  • the high-speed mixing performance was made with reference to whether the granules obtained from the high-speed mixer did not need subsequently milling before entering the compression process which was ranked as excellent. Mixtures exceeding 50% of natural resins were not acceptable for the high-speed mixer due to sticking and lumps creation during the process.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Nutrition Science (AREA)
  • Confectionery (AREA)

Abstract

L'invention concerne une tablette de gomme à mâcher comprimée et un granulé base de gomme pour ladite tablette, qui comprend au moins un élastomère à raison d'environ 0 % à environ 35 % en poids de la base de gomme, au moins deux résines à raison d'environ 15 % à environ 60 % en poids de la base de gomme, des ingrédients de base de gomme. Lesdites résines comprennent une résine naturelle à raison d'environ 5 % à environ 40 % en poids de la base de gomme, une résine synthétique à raison d'environ 10 % à environ 40 % en poids de la base de gomme.
PCT/DK2003/000465 2002-07-02 2003-07-02 Gomme a macher moderee de resine comprimee WO2004004480A1 (fr)

Priority Applications (11)

Application Number Priority Date Filing Date Title
DK03762473T DK1523241T3 (da) 2002-07-02 2003-07-02 Resinmodereret komprimat-tyggegummi
CA2491350A CA2491350C (fr) 2002-07-02 2003-07-02 Gomme a macher moderee de resine comprimee
KR1020047021653A KR101109155B1 (ko) 2002-07-02 2003-07-02 수지로 부드럽게 만든 압축 츄잉 검
JP2004518467A JP5133499B2 (ja) 2002-07-02 2003-07-02 樹脂調整圧縮成形チューインガム
EA200500128A EA008845B1 (ru) 2002-07-02 2003-07-02 Прессованная модифицированная смолой жевательная резинка
DE60321916T DE60321916D1 (de) 2002-07-02 2003-07-02 Komprimierte harz-moderierte kaugummi
AU2003243931A AU2003243931A1 (en) 2002-07-02 2003-07-02 Compressed resin moderated chewing gum
MXPA04012405A MXPA04012405A (es) 2002-07-02 2003-07-02 Goma de mascar comprimida moderada con resina.
EP03762473A EP1523241B1 (fr) 2002-07-02 2003-07-02 Gomme a macher moderee de resine comprimee
US11/028,684 US20050175733A1 (en) 2002-07-02 2005-01-03 Compressed resin moderated chewing gum
US13/352,211 US20120114789A1 (en) 2002-07-02 2012-01-17 Compressed Resin Moderated Chewing Gum

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DKPCT/DK02/00462 2002-07-02
PCT/DK2002/000461 WO2004004478A1 (fr) 2002-07-02 2002-07-02 Plaquette ii de gomme a macher comprimee
DKPCT/DK02/00461 2002-07-02
PCT/DK2002/000462 WO2004004479A1 (fr) 2002-07-02 2002-07-02 Gomme a macher comprimee

Related Child Applications (2)

Application Number Title Priority Date Filing Date
PCT/DK2002/000462 Continuation WO2004004479A1 (fr) 2002-07-02 2002-07-02 Gomme a macher comprimee
US11/028,684 Continuation US20050175733A1 (en) 2002-07-02 2005-01-03 Compressed resin moderated chewing gum

Publications (1)

Publication Number Publication Date
WO2004004480A1 true WO2004004480A1 (fr) 2004-01-15

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JP (1) JP5133499B2 (fr)
KR (1) KR101109155B1 (fr)
AT (1) ATE399467T1 (fr)
AU (1) AU2003243931A1 (fr)
CA (1) CA2491350C (fr)
DE (1) DE60321916D1 (fr)
DK (1) DK1523241T3 (fr)
EA (1) EA008845B1 (fr)
ES (1) ES2309347T3 (fr)
MX (1) MXPA04012405A (fr)
WO (1) WO2004004480A1 (fr)

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WO2006002622A1 (fr) * 2004-07-06 2006-01-12 Gumlink A/S Tablette comprimee de chewing gum
WO2006037343A1 (fr) * 2004-10-08 2006-04-13 Gumlink A/S Produit de confiserie
JP2008504040A (ja) * 2004-06-29 2008-02-14 フェルティン ファルマ アー／エス タバコアルカロイド放出チューインガム
JP2008515408A (ja) * 2004-10-08 2008-05-15 ガムリンク エー／エス チョコレート含有タフィーガム
US7507427B2 (en) 2001-03-23 2009-03-24 Gumlink A/S Coated degradable chewing gum with improved shelf life and process for preparing same
WO2009080022A1 (fr) * 2007-12-20 2009-07-02 Fertin Pharma A/S Tablette de chewing-gum comprimé
WO2009143841A1 (fr) * 2008-05-26 2009-12-03 Fertin Pharma A/S Chewing-gum comprimé et enrobé
WO2009143845A3 (fr) * 2008-05-26 2010-01-21 Fertin Pharma A/S Imprégnation d’arôme d’un noyau de gomme à mâcher
US7900637B2 (en) 2001-06-25 2011-03-08 Niconovum Ab Device and method for the administration of a substance
JP2011057701A (ja) * 2010-12-09 2011-03-24 Fertin Pharma As ニコチンチューインガム使用者に迅速な緩和をもたらす方法
US8137477B2 (en) 2005-03-22 2012-03-20 Gumlink A/S Method of cleaning a surface attached with at least one chewing gum lump
US8137716B2 (en) 2003-05-06 2012-03-20 Gumlink A/S Method for producing chewing gum granules and compressed gum products, and a chewing gum granulating system
US8329235B2 (en) 2003-05-06 2012-12-11 Gumlink A/S Method for producing chewing gum granules, a gum composition extruder and granulating system, and a chewing gum products
US8623331B2 (en) 2007-12-20 2014-01-07 Fertin Pharma A/S Compressed chewing gum tablet
US8722022B2 (en) 2007-12-20 2014-05-13 Fertin Pharma A/S Chewing gum tablet and method of dosing pharmaceutically active ingredients in such chewing gum tablet
US8741348B2 (en) 2002-12-20 2014-06-03 Niconovum Ab Physically and chemically stable nicotine-containing particulate material
US8858919B2 (en) 2004-11-30 2014-10-14 Fertin Pharma A/S Method of providing fast relief to a user of a nicotine chewing gum
US9402809B2 (en) 2006-03-16 2016-08-02 Niconovum Usa, Inc. Snuff composition
US10695292B2 (en) * 2015-06-23 2020-06-30 Fertin Pharma A/S Chewing gum composition for use in alleviation of xerostomia induced by radiotherapy treatment

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KR100713138B1 (ko) * 2006-02-21 2007-05-02 롯데제과주식회사 타정껌의 제조방법
US20070237855A1 (en) * 2006-04-05 2007-10-11 Cadbury Adams Usa Llc Calcium phosphate complex in acid containing confectionery
JP2010252816A (ja) * 2010-08-23 2010-11-11 Gumlink As 圧縮チューインガムタブレット

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US7507427B2 (en) 2001-03-23 2009-03-24 Gumlink A/S Coated degradable chewing gum with improved shelf life and process for preparing same
US7900637B2 (en) 2001-06-25 2011-03-08 Niconovum Ab Device and method for the administration of a substance
US9629832B2 (en) 2002-12-20 2017-04-25 Niconovum Usa, Inc. Physically and chemically stable nicotine-containing particulate material
US8741348B2 (en) 2002-12-20 2014-06-03 Niconovum Ab Physically and chemically stable nicotine-containing particulate material
US8137716B2 (en) 2003-05-06 2012-03-20 Gumlink A/S Method for producing chewing gum granules and compressed gum products, and a chewing gum granulating system
US8329235B2 (en) 2003-05-06 2012-12-11 Gumlink A/S Method for producing chewing gum granules, a gum composition extruder and granulating system, and a chewing gum products
JP2008504040A (ja) * 2004-06-29 2008-02-14 フェルティン ファルマ アー／エス タバコアルカロイド放出チューインガム
US8828361B2 (en) 2004-06-29 2014-09-09 Fertin Pharma A/S Tobacco alkaloid releasing chewing gum
JP2011142926A (ja) * 2004-06-29 2011-07-28 Fertin Pharma As タバコアルカロイド放出チューインガム
US8529875B2 (en) 2004-06-29 2013-09-10 Fertin Pharma A/S Tobacco alkaloid releasing chewing gum
JP2008504828A (ja) * 2004-07-06 2008-02-21 ガムリンク エー／エス 圧縮チューインガムタブレット
WO2006002622A1 (fr) * 2004-07-06 2006-01-12 Gumlink A/S Tablette comprimee de chewing gum
US8734763B2 (en) 2004-07-06 2014-05-27 Gumlink A/S Compressed chewing gum tablet
JP4875616B2 (ja) * 2004-07-06 2012-02-15 ガムリンク エー／エス 圧縮チューインガムタブレット
US9445612B2 (en) 2004-07-06 2016-09-20 Gumlink A/S Compressed chewing gum tablet
AU2005291677B2 (en) * 2004-10-08 2010-10-21 Gumlink A/S Confectionery product
US11135156B2 (en) 2004-10-08 2021-10-05 Fertin Pharma A/S Pharmaceutical tablet for use in administering one or more pharmaceutically active ingredients
JP2012070765A (ja) * 2004-10-08 2012-04-12 Gumlink As チョコレート含有タフィーガム
US10391054B2 (en) 2004-10-08 2019-08-27 Fertin Pharma A/S Pharmaceutical tablet for use in administering nicotine
WO2006037343A1 (fr) * 2004-10-08 2006-04-13 Gumlink A/S Produit de confiserie
US9565867B2 (en) 2004-10-08 2017-02-14 Gumlink A/S Confectionery product comprising low molecular weight polyvinyl acetate
JP2008515408A (ja) * 2004-10-08 2008-05-15 ガムリンク エー／エス チョコレート含有タフィーガム
US8858919B2 (en) 2004-11-30 2014-10-14 Fertin Pharma A/S Method of providing fast relief to a user of a nicotine chewing gum
US8137477B2 (en) 2005-03-22 2012-03-20 Gumlink A/S Method of cleaning a surface attached with at least one chewing gum lump
US9402809B2 (en) 2006-03-16 2016-08-02 Niconovum Usa, Inc. Snuff composition
US11547660B2 (en) 2006-03-16 2023-01-10 Niconovum Usa, Inc. Snuff composition
US11129792B2 (en) 2006-03-16 2021-09-28 Modoral Brands Inc. Snuff composition
US10219999B2 (en) 2006-03-16 2019-03-05 Niconovum Usa, Inc. Snuff composition
US8722022B2 (en) 2007-12-20 2014-05-13 Fertin Pharma A/S Chewing gum tablet and method of dosing pharmaceutically active ingredients in such chewing gum tablet
US9283191B2 (en) 2007-12-20 2016-03-15 Fertin Pharma A/S Compressed chewing gum tablet
WO2009080022A1 (fr) * 2007-12-20 2009-07-02 Fertin Pharma A/S Tablette de chewing-gum comprimé
US8623331B2 (en) 2007-12-20 2014-01-07 Fertin Pharma A/S Compressed chewing gum tablet
US8603440B2 (en) 2007-12-20 2013-12-10 Fertin Pharma A/S Compressed chewing gum tablet
EP2282645B1 (fr) 2008-05-26 2015-04-15 Fertin Pharma A/S Imprégnation d arôme d un noyau de gomme à mâcher
WO2009143841A1 (fr) * 2008-05-26 2009-12-03 Fertin Pharma A/S Chewing-gum comprimé et enrobé
WO2009143845A3 (fr) * 2008-05-26 2010-01-21 Fertin Pharma A/S Imprégnation d’arôme d’un noyau de gomme à mâcher
JP2011057701A (ja) * 2010-12-09 2011-03-24 Fertin Pharma As ニコチンチューインガム使用者に迅速な緩和をもたらす方法
US10695292B2 (en) * 2015-06-23 2020-06-30 Fertin Pharma A/S Chewing gum composition for use in alleviation of xerostomia induced by radiotherapy treatment

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Publication number Publication date
JP5133499B2 (ja) 2013-01-30
EA200500128A1 (ru) 2005-06-30
KR20050026422A (ko) 2005-03-15
ES2309347T3 (es) 2008-12-16
EP1523241A1 (fr) 2005-04-20
DK1523241T3 (da) 2008-10-20
EA008845B1 (ru) 2007-08-31
EP1523241B1 (fr) 2008-07-02
CA2491350C (fr) 2013-03-19
ATE399467T1 (de) 2008-07-15
DE60321916D1 (de) 2008-08-14
MXPA04012405A (es) 2005-09-21
KR101109155B1 (ko) 2012-06-20
JP2005531319A (ja) 2005-10-20
AU2003243931A1 (en) 2004-01-23
CA2491350A1 (fr) 2004-01-15

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